I've recently seen media that only displays a "stop" button in the OSD and the underlying issue was the container (mkv) reporting no duration and thus Kodi has no way to calculate progress. Kodi logs showed this:
Duration: N/A, start: -0.005000, bitrate: N/A
No guarantees your media is the same, but maybe..
Two suggestions for organising things:
Have a look at the "node editor" add-on in the Kodi repo. Nodes are things like "recently added" and "genres" that appear in the GUI, so they combine a node name (can be anything) with saved searches (inclusions and exclusions) and sorting to leverage media metadata in the library DB. I've no idea how that function might be influenced with Emby as the underlying back-end, but it's worth a look.
Kodi Omega also gained a new "versions" capability for movies, allowing e.g. the standard movie, the directors cut, the 3D version, the fan remix, etc. to be stored under a common movie name. Race Weekends are not movies, but some creative abuse of .nfo files and the local file scraper could probably bastardise things into showing a movie name (Race Weekend) with different versions of the movie (Practice, Qualifying, Race, etc.).